Methanol → 3-fluoro-5-(4-methylpiperidin-1-yl)-N-[4-(2H-tetrazol-5-ylmethoxy)-naphthalen-1-yl]-benzamide

HRID 1171423Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1171423
[C:1]([CH2:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([NH:15][C:16](=[O:31])[C:17]2[CH:22]=[C:21]([N:23]3[CH2:28][CH2:27][CH:26]([CH3:29])[CH2:25][CH2:24]3)[CH:20]=[C:19]([F:30])[CH:18]=2)=[CH:7][CH:6]=1)#[N:2].C[Si]([N:36]=[N+:37]=[N-:38])(C)C.C([Sn](=O)CCCC)CCC.CO>C1(C)C=CC=CC=1>[F:30][C:19]1[CH:18]=[C:17]([CH:22]=[C:21]([N:23]2[CH2:24][CH2:25][CH:26]([CH3:29])[CH2:27][CH2:28]2)[CH:20]=1)[C:16]([NH:15][C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]([O:4][CH2:3][C:1]2[N:36]=[N:37][NH:38][N:2]=2)=[CH:6][CH:7]=1)=[O:31]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 59553169HCID 59553169, Verbindung

Produkt 1

HCID 595530853-fluoro-5-(4-methylpiperidin-1-yl)-N-[4-(2H-tetrazol-5-ylmethoxy)-naphthalen-1-yl]-benzamideAusbeute 0 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

N-(4-Cyanomethoxynaphthalen-1-yl)-3-fluoro-5-(4-methylpiperidin-1-yl)-benzamide (54 mg, 129 mmol), trimethylsilylazide (0.1 ml, 760 mmol) and dibutyltin oxide (5 mg) are heated to reflux in anhydrous toluene (3 ml) for 5 hours. After cooling to room temperature methanol (5 ml) is then added and the mixture stirred at room temperature for 30 min. The mixture is then evaporated to dryness and the residue recrystallized from ethyl acetate/hexanes to give 3-fluoro-5-(4-methylpiperidin-1-yl)-N-[4-(2H-tetrazol-5-ylmethoxy)-naphthalen-1-yl]-benzamide as a grey powder (22 mg). 1H NMR 300 MHz (DMSO-d6) 10.3 (s, 1H), 8.32 (dd, 1H, J=8.7 and 2.7 Hz), 7.87 (d, 1H, J=9.3 Hz), 7.54-7.62 (m, 2H), 7.42-7.5 (m, 2H), 7.17 (dd, 1H, J=15.9 and 9.3 Hz), 6.97 (d, 1H, J=13.2 Hz), 5.7 (s, 2H), 3.85 (d, 2H, J=19.8 Hz), 2.77 (m, 2H), 1.5-1.78 (m, 3H), 1.25 (m, 2H), 0.95 (d, 3H, J=6.6 Hz).

Aufarbeitung

  1. additionis then added
  2. customThe mixture is then evaporated to dryness
  3. customthe residue recrystallized from ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-5186335845f24766b96b97933f4dd126
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829560B2

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